Trifluoroacetic acid → HCID 22122185, compound

HRID 1859177Notes

Reaction equation

HRID 1859177 reaction equation
COC1C=C(OC)C=CC=1C[N:6]1[CH2:11][CH2:10][N:9]([CH2:12][C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:14])[C:8](=[O:23])[C:7]1=[O:24].FC(F)(F)C(O)=O.[C:38]1(OC)[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1.C1(C(C2C=CC=CC=2)=[N+]=[N-])C=CC=CC=1>C(OCC)(=O)C.CO>[O:23]=[C:8]1[C:7](=[O:24])[NH:6][CH2:11][CH2:10][N:9]1[CH2:12][C:13]([O:15][CH:16]([C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)=[O:14]

Participants

7

Reactant 4

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 612301,1'-(Diazomethylene)bis(benzene)HCID 53953645HCID 53953645, compound

Product 1

HCID 22122185HCID 22122185, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

A mixture of 10.0 g of benzyl [4-(2,4-dimethoxybenzyl)-2,3-dioxopiperazin-1-yl]acetate, 40 ml of trifluoroacetic acid and 20 ml of anisole was refluxed for 2 hours. After completion of the reaction, the solvent was distilled off under reduced pressure and 20 ml of ethyl acetate and 10 ml of diethyl ether were added to the resulting residue, and the solid was collected by filtration. The solid obtained was dissolved in a mixed solvent of 9 ml of ethyl acetate and 1 ml of methanol, followed by adding thereto 25 ml of a 1 M solution of diphenyldiazomethane in ethyl acetate, and the resulting mixture was stirred at room temperature for 1 hour. The solvent was distilled off under reduced pressure and the resulting residue was purified by a silica gel column chromatography (eluent; chloroform:methanol=10:1) to obtain 6.8 g of diphenylmethyl (2,3-dioxopiperazin-1-yl)acetate as a white foamy substance.

Workup

  1. temperaturewas refluxed for 2 hours
  2. customAfter completion of the reaction
  3. distillationthe solvent was distilled off under reduced pressure and 20 ml of ethyl acetate and 10 ml of diethyl ether
  4. additionwere added to the resulting residue
  5. filtrationthe solid was collected by filtration
  6. customThe solid obtained
  7. additionby adding
  8. distillationThe solvent was distilled off under reduced pressure
  9. customthe resulting residue was purified by a silica gel column chromatography (eluent; chloroform:methanol=10:1)

Sources & evidence

ORD record
ord-41fc9d3e476e42b7805007885e18993a
Source dataset
uspto-grants-2000_11
Patent number
US06153613

Reaction notes

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